At some point, life evolves from being asked “What do you want to be when you grow up” -- astronaut pizza chef veterinarian, of course -- to “So, what do you do?”

The people who want to hire you need to know if you’re for them, and you need to know if you even want to take the work…myself included.

So, like you, I get asked this question a lot. The problem is, my answer is a little complicated.

In one camp, we have Billboard People. These are people who can say what they do in a pithy little statement or with an acronym, because they do a thing you already understand or solve a well-established problem. And there are Podcast People, who need some space for nuance and relationship-building. 

I am a Podcast Person. But I don’t have one of those, so this newsletter will have to do.

It’s easier to start with who I’m for, because the job-title version gets murky fast. My clients often use shorthand, like “she’s my CFO,” because there isn’t a tidy word for our work situationship. We all need to use numbers. We all need to work through growth and feelings. Neither of those things box me into CFO or “business therapy.”

So, we’ll start with the who: 

I help self-funded founders who want to build profitable, sustainable, values-aligned companies. 

When I say “self-funded,” I’m not saying you can’t be someone who’s never taken out a loan or had a business partner. All it means is you’re not going out to raise money. If you’re not seeking venture funding, we’re good. 

If you have a distinct opinion of how you want to make the world a better place with your work, then we’re even better.

1) Strategy engagement (finite)

This is for people who have started something, but they’re feeling stuck. They can’t find the path to where they want to go without losing their why. 

They know they’ve got a good business in front of them, but it’s not working for them right now. There are too many decisions. They know what they need to get paid and what they don’t want to do, but they can’t turn that into a plan that they feel ready to act upon.

So we figure out: 

We do the work over a few weeks so you have time to reflect and make sure it works for you. You walk away with direction and some clear, impactful actions toward your goals.

2) Fractional general management

Some clients want me to stay on and help implement the plan. That’s where my role gets murky, but in a good way.

Once you’re growing, hiring, setting up in another state, and dealing with compliance, legal, operations, people stuff, finance, supply chain, and nexus, small businesses get complex very fast. You need to level up, but you don’t have time or money to manage six domain experts.

That’s why I call it “fractional general management.” With our partners, we can be the team captain and your partner for managing all the financial, administrative, and probably boring-but-necessary stuff it takes to grow and run your company.

This is a short answer, but it encompasses a lot. 

“I need to make this business work. I kind of hate it right now.” 

Under that is usually: 

“I know there’s a good business here, but I can’t see the path. I have too many options. I don’t know what to do next. I can’t get from my messy pile of thoughts and tasks to a meaningful plan.”

And that’s where we get to work.

I’m not a coach.

I know lots of great coaches, many with mental health training, which I think is important. For me, I don’t like telling people what they should do and then letting them wander off into the world to figure it out. 

Many entrepreneurs use coaching as implied permission to carry out a plan that they’ve been advised against, or they confuse a coach with a therapist. That really isn’t what I do. We problem-solve, and we build things together. 

And yes, people ask if there’s a way to just “get my ideas” without engaging with me so intensely. Absolutely! You’re reading it. There’s a whole free archive of eight years of my opinions about what you should do. 

My best work happens when I’m integral to the function of your company, doing the hard stuff that most people want to walk away from. I moved to this freemium model because if you’re paying me, I want to be a partner in running your company.

Usually people can give you an answer for your business from their single lane of expertise. 

Finance people will protect your cash flow or balance sheet. Lawyers will consider the worst downside risks. Operators will push for norms and systems. And most everybody will cover their booties to limit their liability while earning your fees. 

Now we have some pretty good AI, which, if you’re using it right, you can ask to take on these roles. For example, you prompt, “You are a CFO of an early stage company.”  You will get a very good “what a CFO would say” answer. Then you ask what a COO would say, then what a CMO would say, and you end up with three different answers. Your next prompt, “Now what the f*** do I do?” isn’t going to end well.

The difference is I’ve had all of these jobs. I’ve managed a lot of companies from figuring out their first dollar to up to $25 million. And here’s what I’ll ask you: 

Only you can answer these questions. One more piece: I’ve been a personal wealth manager, which means I can speak to smart ways to accomplish your goals.

When I work with clients, I’m managing toward the end goal with the guard rails that you define. We’re not just talking about what you could do. We’re making decisions, getting you through the messy parts, and keeping you in the entrepreneurial game while you learn and grow. 

What does that look like? It’s different for each client.

But every single client has a moment when we’re in the shit. No matter how well we plan, everybody has their crucible leadership moment.

Day-to-day cash flow. A crunchy month or quarter, when every decision and dollar spent matters. The job is sustaining the business, but also supporting you as you manage your way through. You’re the CEO. I will tell you what I think. If I say Door No. 1 and you choose Door No. 2,  we’re on the ride with you. After 12 years of working with founders, I’ve learned that you can’t cheat a CEO out of the experiences they need to have. You can just be there with your whole heart, support them, and help them find their way to the other side. 

So if what you want is someone to give you permission for something you were going to do no matter what, I am not your person.

But if you want a partner who can help you decide what to do, help you actually do it, and stay steady with you through the messy parts inside your business, that’s what I’m here for.

And if you’d like to set up a conversation to see if I’m the right person to work with you, I’d love to talk to you. Otherwise, I am genuinely happy you’re here as a subscriber. 

This week, it’s crunch time: are you filing on time or taking an extension? 

A quick reminder, the personal retirement contribution deadline cannot be extended. The business contribution deadline can. And any ticking clocks stop on the day you file your taxes.

The E-shaped economy. Move over, K-shape, we bought a vowel. In the latest sign  that things aren’t going so great, Costco partnered with luxury brand Off-White to offer $400 hoodies for US$60, starting in Canadian locations. Costco is leaning into the new E in economy, in which even relatively well-off households are reconsidering spending. In the E-shaped economy, the top tier (5-10% of households) continues to spend flagrantly. The next tier (10-30%) is proceeding with caution, spending only on bargains -- your classic Costco shopper. And the lowest tier (which is a majority of the US population) is just trying to make ends meet. Consumer sentiment is currently near historic lows seen in 2020 and 1980, the last time the US faced an oil crisis. (If you’re a glutton for punishment, click on March 2024 in that chart and brace for the reflexive head slap.)

Texts making me look dopey. Have you noticed that a text you sent changed after your last look, and some nonsense was transmitted? You’re not alone -- the latest iOS update acknowledges this issue is real and offers some updates. But you might have to delete your error-filled “learned” library and add some proper nouns to your contacts. 

Student loans. Back in August, loans in forbearance under SAVE plans started to accrue interest. While you can wait, from July 1, you’ll have 90 days to opt into a new repayment plan and start paying your loans again. Both repayment options will offer forgiveness after a period of payment. The updated income-based repayment (IBR) program requires that you pay a percentage of your disposable income, and even those with no income are required to pay at least $10 a month. With 7.2 million Americans still in forbearance, this could be another hit to consumer spending in September. 

Agency and the future. Each year, I’ve reviewed futurist Amy Webb’s SXSW Trend Report. This year, her firm retired trends and moved to a whopping 300+ page Convergence Outlook. Before you tackle the report, watch her SXSW talk about the top 3 convergences: human augmentation, unlimited labor, and emotional outsourcing. If you’re anxious about your working future, make time for this one.

ICYMI, here are resources you should know about:

Michael B. Jordan is not only an Oscar winner, he’s also a great reminder that growth is not free. He took on a minority equity partner for access, money, and connections. When they started pushing the company in a direction he did not want, he bought them out to regain control. A reminder to be clear on the price of growth, because it’s hard to buy back control.

Women’s History Month just ended, and I love this one: United’s top pilot for 2026 is a woman. She didn’t frame it as “yay, I made it.” She framed it as “other women went through stuff so I could be here, and I want to make it possible for the next group.” That pattern is showing up everywhere. The WNBA just rewrote their collective bargaining agreement (CBA) and made sure there was money for the women who built the league. They didn’t have to do that, but they did. (With the help of a Nobel Prize-winning female economist.) Respect those who made your future possible, and do the same for someone else.